In one aspect, this invention pertains to aldehyde and alcohol compositions, preferably, derived from seed oils. In another aspect, this invention pertains to a process of preparing the aldehyde composition via hydroformylation of an unsaturated fatty acid or unsaturated fatty acid ester feedstock derived from seed oils. Likewise, this invention also pertains to a process of preparing the alcohol composition via hydroformylation and subsequent hydrogenation of an unsaturated fatty acid or unsaturated fatty acid ester feedstock derived from seed oils.
Alcohol compositions are useful in that they can be converted into polyols that find utility in the manufacture of polyurethanes. Aldehyde compositions are useful in that they can be converted via hydrogenation into alcohols or amines, which in turn can be converted into polyols and polyamines for the manufacture of polyurethanes. Aldehydes can also be converted into carboxylic acids, hydroxy acids, amino alcohols, amino acids, and other commercially useful derivatives.
Currently, industry-wide efforts are underway to replace petroleum-based chemical feedstocks with non-petroleum-based chemical feedstocks. Seed oils, which comprise a mixture of saturated and unsaturated fatty acid esters, provide a promising source of renewable non-petroleum-based feedstocks for industrial utilization. Aldehydes and alcohols derived from seed oils have the potential to be converted into many useful industrial chemicals, notably, polyols for use in polyurethanes.
To be useful in polyurethane manufacture non-petroleum-based polyols should provide for similar reactivity and urethane end-product at acceptable cost, as compared with conventional petroleum-based polyols. Non-petroleum-based polyols may also provide opportunities for preparing unconventional polyurethane products having novel properties. The properties of polyurethanes are known to vary depending upon the polyol composition employed during polyurethane manufacture. Non-petroleum-based aldehyde and alcohol compositions should be engineered such that the polyols derived therefrom yield polyurethanes of acceptable properties for their desired end-use. Polyols to be used in manufacture of polyurethane slab stock flexible foams, for example, should provide for acceptable cross-link density, that is, cross-link density neither too high nor too low; else the foam has unacceptable rigidity or flexibility. The invention described herein pertains particularly to aldehyde and alcohol compositions that are preferably derived from seed oils and that provide for polyols having acceptable properties for the manufacture of polyurethane slab stock flexible foams.
Prior art, as exemplified by U.S. Pat. No. 3,787,459, discloses a process for converting unsaturated vegetable oil materials via hydroformylation into formyl (aldehyde) products. Disclosed vegetable oils include soybean, linseed, and safflower oils, and their derivatives. Typically, the process appears to be operated to conversions of greater than 90 percent total unsaturates. As best as can be determined, the formyl composition disclosed in U.S. Pat. No. 3,787,459 consists of from 24 to 92 percent monoformyl and from 17 to 75 percent diformyl products.
Other prior art, such as EP-B1-711748, discloses a process for preparing di- and polyformylcarboxylic esters by hydroformylation of esters of multiply unsaturated fatty acids, such as soybean oil, sunflower oil, linseed oil, and other vegetable oils. The conversion of feedstock appears to range from roughly 55 to 100 percent by weight. The resulting aldehyde composition, as illustrated in the examples, appears to comprise from 23 to 35 percent monoformyl, from 12 to 31 percent diformyl, and from 3 to 29 percent triformyl products, by weight.
Yet other prior art, illustrated by U.S. Pat. No. 5,177,228, discloses the hydroformylation of an unsaturated fatty acid ester, such as methyl oleate, to a monoformyl fatty acid ester, such as methylformyl stearate.
In view of the above, it would be advantageous to discover aldehyde and alcohol compositions that can be derived from renewable non-petroleum-based feedstocks, such as seed oils. Moreover, it would be advantageous to discover such aldehyde and alcohol compositions that can also be converted into polyols having acceptable properties for use in polyurethane slab stock flexible foam applications.